Simultaneous Cyclization and Derivatization of Peptides Using Cyclopentenediones

Unprotected linear peptides containing N-terminal cysteines and another cysteine residue can be simultaneously cyclized and derivatized using 2,2-disubstituted cyclopentenediones. High yields of cyclic peptide conjugates may be obtained in short reaction times using only a slight excess of the cyclo...

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Bibliographic Details
Published in:Organic letters 2017-03, Vol.19 (5), p.992-995
Main Authors: Brun, Omar, Archibald, Lewis J, Agramunt, Jordi, Pedroso, Enrique, Grandas, Anna
Format: Article
Language:English
Subjects:
Cisteïna
Cysteine
Estructura molecular
Molecular structure
Peptides
Pèptids
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Summary:Unprotected linear peptides containing N-terminal cysteines and another cysteine residue can be simultaneously cyclized and derivatized using 2,2-disubstituted cyclopentenediones. High yields of cyclic peptide conjugates may be obtained in short reaction times using only a slight excess of the cyclopentenedione moiety under TEMPO catalysis and in the presence of LiCl.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b03825